Synthesis and in vitro antiproliferative evaluation of novel drimane oxepinyl triazoles from labdane diterpene sclareol

Kristina G, Karl-Heinz B, Gisbert S. Scaffold diversity of natural products: inspiration for combinatorial library design. Nat Prod Rep. 2008;25:892–904.

Article  Google Scholar 

Sasadhar M, Debjit D. Chemical derivatization of natural products: semisynthesis and pharmacological aspects—a decade update. Tetrahedron. 2020;78:131801.

Google Scholar 

Jansen DJ, Shenvi RA. Synthesis of medicinally relevant terpenes: reducing the cost and time of drug discovery. Future Med Chem. 2014;6:1127–48.

Article  CAS  PubMed  Google Scholar 

Günnewich N, Higashi Y, Feng X, Choi K-B, Schmidt J, Kutchan TM. A diterpene synthase from the clary sage Salvia sclarea catalyzes the cyclization of geranylgeranyl diphosphate to (8R)-hydroxy-copalyl diphosphate. Phytochemistry. 2013;91:93–99.

Article  PubMed  Google Scholar 

Yang S, Tian H, Sun B, Liu Y, Hao Y, Lv Y. One-pot synthesis of (−)-Ambrox. Sci Rep. 2016;6:32650.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Jameel S, Bhat KA. Sclareol: isolation, structural modification, biosynthesis, and pharmacological evaluation—a review. Pharm Chem J. 2024;57:1568–79.

Article  CAS  Google Scholar 

Jansen BJM, Groot A. Occurrence, biological activity and synthesis of drimane sesquiterpenoids. Nat Prod Rep. 2004;21:449–77.

Article  CAS  PubMed  Google Scholar 

Zhou J, Xie X, Tang H, Peng C, Peng F. The bioactivities of sclareol: a mini-review. Front Pharmacol. 2022;13:1014105.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Rehman S, Rah B, Lone SH, Rasool RU, Farooq S, Nayak D, et al. Design and synthesis of antitumor heck-coupled sclareol analogues: modulation of BH3 family members by SS-12 in autophagy and apoptotic cell death. J Med Chem. 2015;58:3432–44.

Article  CAS  Google Scholar 

Jampilek J. Heterocycles in medicinal chemistry. Molecules. 2019;24:3839.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Fominova K, Diachuk T, Granat D, Savchuk T, Vilchynskyi V, Svitlychnyi O, et al. Oxa-spirocycles: synthesis, properties and applications. Chem Sci. 2021;12:11294–305.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Nguyen AT, Kim HK. Recent advances in synthetic routes to azacycles. Molecules. 2023;28:2737.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Ugwu DI, Eze FU, Ezugwu JA, Attah SI, Ugwu MC, Ekoh OC, et al. Chemotherapeutic importance of oxepines. Int J Chem Sci. 2020;19:401.

Google Scholar 

Khandelwal R, Vasava M, Abhirami RB, Karsharma M. Recent advances in triazole synthesis via click chemistry and their pharmacological applications: a review. Bioorganic Med Chem Lett. 2024;112:129927.

Article  CAS  Google Scholar 

Guo HY, Chen ZA, Shen QK, Quan ZS. Application of triazoles in the structural modification of natural products. J Enzyme Inhib Med Chem. 2021;36:1115–44.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Sinka V, Martín VS, Cruz DA, Padrón JI. Synthesis of seven membered oxacycles: recent developments and new approaches. Eur J Org Chem. 2020;43:6704–17.

Article  Google Scholar 

Mir SA, Mir SM, Hussain G, Bharitkar YP, Malik FA, Yousuf SK. Suzuki coupling-based synthesis and in vitro cytotoxic evaluation of C-2 aryl derivatives of Withaferin A. Steroids. 2023;195:109246.

Article  Google Scholar 

Bouanou H, Gil JA, Alvarez-Manzaneda R, Chahboun R, Alvarez-Manzaneda E. Oxidative coupling of (−)-Sclareol and related diols leading to oxepane terpenoids. J Org Chem. 2016;81:10002–8.

Article  CAS  PubMed  Google Scholar 

Dimas K, Hatziantoniou S, Tseleni S, Khan H, Georgopoulos A, Alevizopoulos K, et al. Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice. Apoptosis. 2007;12:685–94.

Article  CAS  PubMed  Google Scholar 

Bharate SB, Kumar V, Jain SK, Mintoo MJ, Guru SK, Nuthakki VK, et al. Discovery and preclinical development of IIIM-290, an orally active potent cyclin-dependent kinase inhibitor. J Med Chem. 2018;61:1664–87.

Article  CAS  PubMed  Google Scholar 

Kumar A, Singh B, Mahajan G, Sharma PR, Bharate SB, Mintoo MJ, et al. A novel colchicine-based microtubule inhibitor exhibits potent antitumor activity by inducing mitochondrial-mediated apoptosis in MIA PaCa-2 pancreatic cancer cells. Tumor Biol. 2016;37:13121–36.

Article  CAS  Google Scholar 

Wani A, Gupta M, Ahmad M, Shah AM, Ahsan AU, Qazi PH, et al. Alborixin clears amyloid-β by inducing autophagy through PTEN-mediated inhibition of the AKT pathway. Autophagy. 2019;15:1810–1828.

Article  CAS  PubMed  PubMed Central  Google Scholar 

留言 (0)

沒有登入
gif